First, don't assume you're going to crash your first car.
Second, the MK3 Supra is nothing special. It was more a luxury car than a sports car. The spectacularness of the MK4 may trickle down to the MK3 in terms of raising the price a bit, but the performance of the MK3 doesn't warrant it. Eight grand will get you a newer, better used car than a 15-20 year old Supra.
Whatever you buy, use edmunds.com True Market Value to determine price. Kelly Blue Book is the seller's friend, not the buyer's.